JPH0510130B2 - - Google Patents
Info
- Publication number
- JPH0510130B2 JPH0510130B2 JP59183519A JP18351984A JPH0510130B2 JP H0510130 B2 JPH0510130 B2 JP H0510130B2 JP 59183519 A JP59183519 A JP 59183519A JP 18351984 A JP18351984 A JP 18351984A JP H0510130 B2 JPH0510130 B2 JP H0510130B2
- Authority
- JP
- Japan
- Prior art keywords
- protein
- alanine
- aliphatic alcohol
- emulsifier
- producing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 235000018102 proteins Nutrition 0.000 claims description 89
- 102000004169 proteins and genes Human genes 0.000 claims description 89
- 108090000623 proteins and genes Proteins 0.000 claims description 89
- 239000003995 emulsifying agent Substances 0.000 claims description 67
- 235000004279 alanine Nutrition 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 34
- -1 alanine aliphatic alcohol ester Chemical class 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 19
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 17
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
- 108010059378 Endopeptidases Proteins 0.000 claims description 12
- 102000005593 Endopeptidases Human genes 0.000 claims description 12
- 108010010803 Gelatin Proteins 0.000 claims description 12
- 229920000159 gelatin Polymers 0.000 claims description 12
- 239000008273 gelatin Substances 0.000 claims description 12
- 235000019322 gelatine Nutrition 0.000 claims description 12
- 235000011852 gelatine desserts Nutrition 0.000 claims description 12
- 238000000354 decomposition reaction Methods 0.000 claims description 10
- 239000004365 Protease Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 108090000526 Papain Proteins 0.000 claims description 5
- 101710097834 Thiol protease Proteins 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 210000004899 c-terminal region Anatomy 0.000 claims description 5
- 238000011033 desalting Methods 0.000 claims description 5
- 108010013296 Sericins Proteins 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 235000019834 papain Nutrition 0.000 claims description 4
- 229940055729 papain Drugs 0.000 claims description 4
- 102000035195 Peptidases Human genes 0.000 claims description 3
- 108091005804 Peptidases Proteins 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 244000298697 Actinidia deliciosa Species 0.000 claims description 2
- 235000009436 Actinidia deliciosa Nutrition 0.000 claims description 2
- 108010004032 Bromelains Proteins 0.000 claims description 2
- 108090000712 Cathepsin B Proteins 0.000 claims description 2
- 102000004225 Cathepsin B Human genes 0.000 claims description 2
- 108090001069 Chymopapain Proteins 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
- 102000008186 Collagen Human genes 0.000 claims description 2
- 108090000942 Lactalbumin Proteins 0.000 claims description 2
- 102000004407 Lactalbumin Human genes 0.000 claims description 2
- 108010058846 Ovalbumin Proteins 0.000 claims description 2
- 108010071390 Serum Albumin Proteins 0.000 claims description 2
- 102000007562 Serum Albumin Human genes 0.000 claims description 2
- ISWQCIVKKSOKNN-UHFFFAOYSA-L Tiron Chemical compound [Na+].[Na+].OC1=CC(S([O-])(=O)=O)=CC(S([O-])(=O)=O)=C1O ISWQCIVKKSOKNN-UHFFFAOYSA-L 0.000 claims description 2
- 229920002494 Zein Polymers 0.000 claims description 2
- 108010055615 Zein Proteins 0.000 claims description 2
- 235000019835 bromelain Nutrition 0.000 claims description 2
- 239000005018 casein Substances 0.000 claims description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 2
- 235000021240 caseins Nutrition 0.000 claims description 2
- 229960002976 chymopapain Drugs 0.000 claims description 2
- 229920001436 collagen Polymers 0.000 claims description 2
- 229940092253 ovalbumin Drugs 0.000 claims description 2
- 235000019419 proteases Nutrition 0.000 claims description 2
- 108010078692 yeast proteinase B Proteins 0.000 claims description 2
- 239000005019 zein Substances 0.000 claims description 2
- 229940093612 zein Drugs 0.000 claims description 2
- 108010076119 Caseins Proteins 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 86
- 229960003767 alanine Drugs 0.000 description 54
- 229940024606 amino acid Drugs 0.000 description 25
- 235000001014 amino acid Nutrition 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 230000001804 emulsifying effect Effects 0.000 description 17
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 16
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 16
- 150000001413 amino acids Chemical class 0.000 description 16
- 238000006911 enzymatic reaction Methods 0.000 description 14
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- UCCMBYBOOAOUMZ-SFHVURJKSA-N hexadecyl (2s)-2-aminopropanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)[C@H](C)N UCCMBYBOOAOUMZ-SFHVURJKSA-N 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
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- 238000003756 stirring Methods 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 229960000541 cetyl alcohol Drugs 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
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- 238000001914 filtration Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 238000000502 dialysis Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001165 hydrophobic group Chemical group 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- 229940088598 enzyme Drugs 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- 229960003136 leucine Drugs 0.000 description 4
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- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
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- 125000005907 alkyl ester group Chemical group 0.000 description 3
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- IJQSPVNIBARJGC-BDQAORGHSA-N 4-methylbenzenesulfonic acid;octadecyl (2s)-2-aminopropanoate Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CCCCCCCCCCCCCCCCCCOC(=O)[C@H](C)N IJQSPVNIBARJGC-BDQAORGHSA-N 0.000 description 2
- XFVHNODEIQTQOH-NTISSMGPSA-N 4-methylbenzenesulfonic acid;tetradecyl (2s)-2-aminopropanoate Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CCCCCCCCCCCCCCOC(=O)[C@H](C)N XFVHNODEIQTQOH-NTISSMGPSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 2
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- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
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- CNRMCFSNURPKJN-FERBBOLQSA-N hexadecyl (2s)-2-aminopropanoate;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.CCCCCCCCCCCCCCCCOC(=O)[C@H](C)N CNRMCFSNURPKJN-FERBBOLQSA-N 0.000 description 2
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
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- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
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- 208000017520 skin disease Diseases 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PFYGVQNQQVGRSE-IBGZPJMESA-N tetradecyl (2s)-2-amino-4-methylpentanoate Chemical compound CCCCCCCCCCCCCCOC(=O)[C@@H](N)CC(C)C PFYGVQNQQVGRSE-IBGZPJMESA-N 0.000 description 1
- OGRCQGKJWFJROA-INIZCTEOSA-N tetradecyl (2s)-2-aminopropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)[C@H](C)N OGRCQGKJWFJROA-INIZCTEOSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/30—Proteins; Protein hydrolysates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/645—Proteins of vegetable origin; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- General Preparation And Processing Of Foods (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59183519A JPS6161624A (ja) | 1984-09-01 | 1984-09-01 | 蛋白質系乳化剤の製法 |
| US07/153,561 US4826818A (en) | 1983-10-26 | 1984-10-26 | Proteinaceous emulsifier, process for preparing same and emulsion type cosmetic compositions containing same |
| PCT/JP1984/000512 WO1985001890A1 (fr) | 1983-10-26 | 1984-10-26 | Agent emulsifiant proteique, son procede de preparation et preparation cosmetique emulsifiee le contenant |
| DE8484903982T DE3482551D1 (de) | 1983-10-26 | 1984-10-26 | Proteinhaltiges emulgiermittel, dessen herstellung und dieses enthaltende emulgierte kosmetische zusammensetzung. |
| EP84903982A EP0160103B1 (fr) | 1983-10-26 | 1984-10-26 | Agent emulsifiant proteique, son procede de preparation et preparation cosmetique emulsifiee le contenant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59183519A JPS6161624A (ja) | 1984-09-01 | 1984-09-01 | 蛋白質系乳化剤の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6161624A JPS6161624A (ja) | 1986-03-29 |
| JPH0510130B2 true JPH0510130B2 (fr) | 1993-02-08 |
Family
ID=16137264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59183519A Granted JPS6161624A (ja) | 1983-10-26 | 1984-09-01 | 蛋白質系乳化剤の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6161624A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3795669T3 (pl) * | 2009-06-29 | 2024-03-18 | Inolex Investment Corporation | Nieropopochodne emulgatory kationowe będące estrami zobojętnionych aminokwasów oraz pokrewne kompozycje i sposoby |
-
1984
- 1984-09-01 JP JP59183519A patent/JPS6161624A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6161624A (ja) | 1986-03-29 |
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